Sodium hydride → N-formyl-N-(pyridin-2-yl)formamide

HRID 2041813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041813
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:10]=[O:11].[CH:12](OC(=O)C)=[O:13]>C1COCC1>[CH:10]([N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[CH:12]=[O:13])=[O:11]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 75269Acetic-formic anhydrideHCID 3781604N-(pyridin-2-yl)formamide

Produkt 1

HCID 59583153N-formyl-N-(pyridin-2-yl)formamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (10.8 g, 60 wt %, 0.27 mol) in 50 mL of THF was added dropwise a solution of N-(pyridine-2-yl)formamide (22.4 g, 0.18 mol) in 250 mL of THF. When the addition was complete, the reaction was stirred at room temperature for 30 minutes and then cooled in an ice/salt bath. The acetic formic anhydride ethereal solution from the previous step was added in one portion. The resulting mixture was stirred in the ice bath for 30 minutes and then overnight at room temperature. The mixture was poured into 1 L of ice/water and extracted with 3×250 mL of CH2Cl2. The combined organic extracts were washed with 2×250 mL of H2O, dried and evaporated to give 33.2 g of solid. The crude product was column chromatographed (silica gel) eluting with 100% CH2Cl2 followed by 90:10 CH2Cl2:EtOAc. 14.2 g of product was isolated as a white solid.

Aufarbeitung

  1. additionWhen the addition
  2. temperaturecooled in an ice/salt bath
  3. customovernight
  4. customat room temperature
  5. extractionextracted with 3×250 mL of CH2Cl2
  6. washThe combined organic extracts were washed with 2×250 mL of H2O
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e3f14fc30e2d4ba5a5d5209aee2ee9d2
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586203B2

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